3'-Nitro-[1,1'-biphenyl]-4-ol → (+/-)-1-(3'-Nitrobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600918Notes

Reaction equation

HRID 1600918 reaction equation
Cl[CH2:2][CH:3]([OH:12])[CH2:4][CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[N+:13]([C:16]1[CH:17]=[C:18]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14]>C(O)C.[OH-].[Na+]>[N+:13]([C:16]1[CH:17]=[C:18]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:2][CH:3]([OH:12])[CH2:4][CH2:5][C:6]3[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=3)=[CH:24][CH:23]=2)[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 124650873'-Nitro-[1,1'-biphenyl]-4-olHCID 22465338HCID 22465338, compound

Product 1

HCID 21830655(+/-)-1-(3'-Nitrobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of (±)-α-(chloromethyl)-3-pyridinepropanol (0.80 g) in ethanol (10 ml) was added to a refluxing solution of 3'-nitrobiphenyl-4-ol (1.40 g) in ethanol (20 ml) and aqueous sodium hydroxide (1.4 M, 5 ml) over 30 minutes. The solution was heated at reflux for a further hour and then was cooled to room temperature. The reaction mixture was concentrated under reduced pressure and the residue purified by column chromatography over silica eluting with chloroform:ethanol (49:1 to 24:1) to give a yellow solid after trituration with ether (0.332 g).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for a further hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue purified by column chromatography over silica eluting with chloroform:ethanol (49:1 to 24:1)
  5. customto give a yellow solid after trituration with ether (0.332 g)

Sources & evidence

ORD record
ord-c6ab8984e17b4674a77991bc048a0e02
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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